It is the overall objective of this research program to develop an efficient procedure for the construction of jatrophone(1) and related 3(2H)-furanone derivatives which appear to be potential antitumor agents. Jatrophone, an architecturally interesting diterpene possessing a macrocyclic ring skeleton and a spiro 3(2H)-furanone functionality, is known to possess significant inhibitory activity against carcinoma 180, Lewis lung carcinoma, P-388 lymphocytic leukemia in the mouse, and Walker 256 intramuscular carcinosarcoma in the rat. (Cancer Chemother. Rep., 25, 1 (1962)). Our synthetic approach to jatrophone calls initially for elaboration of a spiro 3(2H)-furanone derivative onto which the macrocyclic ring will be constructed. Four synthetic strategies for construction and closure of the required macrocyclic ring are envisioned. These strategies are termed: A) The tosylate displacement sequence; B) the aldol condensation sequence; C) the chain homologation sequence; and D) the macrocyclic lactone sequence. Concomitant with the development of our synthetic approach to jatrophone, we plan to explore the chemistry of the 3(2H)-furanone functionality. This line of inquiry is significant to our research program since the 3(2H)-furanone ring system is central to the jatrophone molecule. Initially, the following four topics will be examined: A) Synthesis of the parent 3(2H)-furanone ring system and related simple derivatives; B) utilization of the 3(2H)-furanone functionality as a potential Michael acceptor; C) 3(2H)-furanone derivatives as potential dienophiles and dipolarophiles; and D) preparation of 2-methylene-3(2H)-furanone, a possible antitumor agent.